Trifluoroacetic acid → Trifluoroacetic acid

HRID 590858Notes

Reaction equation

HRID 590858 reaction equation
[C:1]1([C@H:7]([NH:9][C:10](=[O:45])[NH:11][C:12]2[N:17]=[CH:16][C:15]3[C:18]([NH:40][C:41](=[O:44])[O:42][CH3:43])=[N:19][N:20](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:14]=3[CH:13]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([SiH](CC)CC)C.[C:53]([OH:59])([C:55]([F:58])([F:57])[F:56])=[O:54]>>[C:1]1([C@H:7]([NH:9][C:10](=[O:45])[NH:11][C:12]2[N:17]=[CH:16][C:15]3[C:18]([NH:40][C:41](=[O:44])[O:42][CH3:43])=[N:19][NH:20][C:14]=3[CH:13]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:53]([OH:59])([C:55]([F:58])([F:57])[F:56])=[O:54]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 73505443HCID 73505443, compound

Product 2

HCID 6422Trifluoroacetic acidYield 57.5%HCID 118380794HCID 118380794, compound

Procedure

(R)-methyl (6-(3-(1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate (0.622 mmol) was taken up in TFA (5 ml) and the reaction mixture stirred at room temperature for 1 h. Triethylsilane (0.113 ml, 0.705 mmol) was added drop wise, and the reaction mixture stirred for an additional 5 minutes. The mixture was concentrated, re-dissolved in DMSO (1.5 mL) and submitted for purification by mass-triggered preparative HPLC to afford (R)-methyl (6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate, TFA (190 mg, 0.406 mmol, 57.5% yield) as a white solid. MS ESI calc'd. For C17H19N6O3 [M+H]+ 355. found 355. 1H NMR (600 MHz, DMSO): 12.69 (br s, 1H); 10.39 (br s, 1H); 9.27 (br s, 1H); 8.95 (s, 1H); 7.76 (br s, 1H); 7.43 (s, 1H); 7.31 (d, J=4.5 Hz, 4H); 7.21 (m, 1H); 4.85 (t, J=7.3 Hz, 1H); 3.68 (s, 3H); 1.39 (d, J=6.9 Hz, 3H).

Workup

  1. stirringthe reaction mixture stirred for an additional 5 minutes
  2. concentrationThe mixture was concentrated
  3. dissolutionre-dissolved in DMSO (1.5 mL)
  4. customsubmitted for purification by mass-triggered preparative HPLC

Sources & evidence

ORD record
ord-7b2bc56d5970429ab6a098d0e0f5d1c8
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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